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ergometrine

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A monocarboxylic acid amide that is lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on the uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vessels in the uterine wall are compressed and blood flow reduced.

Term info

Label

ergometrine

Synonyms
  • Ergometrine
  • N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-9,10-didehydroergoline-8beta-carboxamide
database cross reference
Subsets

3_STAR

INN
ergometrina [ ChemIDplus ]

INN
ergometrine [ WHO_MedNet ]

IUPAC NAME
N-[(2S)-1-hydroxypropan-2-yl]-6-methyl-9,10-didehydroergoline-8beta-carboxamide [ IUPAC ]

INN
ergometrine [ ChemIDplus ]

INN
ergometrinum [ ChemIDplus ]

charge

0

formula

C19H23N3O2

has alternative id

CHEBI:296351

has obo namespace

chebi_ontology

has related synonym

ergometrina, ergobasine, ergometrine, 9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamide, D-lysergic acid-L-propanolamide, ergometrinum, (6aR,9R)-7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid ((S)-2-hydroxy-1-methyl-ethyl)-amide, ergotocine, margonovine, D-lysergic acid 1-hydroxymethylethylamide, N-(alpha-(hydroxymethyl)ethyl)-D-lysergamide, N-(2-Hydroxy-1-methylethyl)-D-(+)-lysergamide, Ergonovine, 9,10-didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamide, [8beta(S)]-9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8-carboxamide

id

CHEBI:4822

inchi

InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1

inchikey

WVVSZNPYNCNODU-XTQGRXLLSA-N

mass

325.40480

monoisotopicmass

325.17903

smiles

C[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34